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<h1><a href="https://archiveofourown.org/works/23822449">Business of Pleasure</a> by <a class='authorlink' href='https://archiveofourown.org/users/SinQueen69/pseuds/SinQueen69'>SinQueen69</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>Requests [73]</td></tr>

<tr><td><b>Category:</b></td><td>Teen Wolf (TV)</td></tr>

<tr><td><b>Genre:</b></td><td>Anal Gaping, Anal Sex, Body Worship, Bondage, Bottom Derek Hale, CEO Derek Hale, Collar, Come Marking, Creampie, Desk Sex, Dirty Talk, Dom Stiles Stilinski, Dom/sub, Don't copy to another site, Edging, Forniphilia, Gag, Human Furniture, Humiliation, Jockstrap Kink, Leather Kink, Light Masochism, M/M, Nipple Clamps, Nipple Play, Object Insertion, Object Penetration, Office Sex, Oral Sex, Orgasm Control, Praise Kink, Public Sex, Sub Derek Hale, Teasing, Top Stiles Stilinski, bdsm club, blindfold, makeshift leash, spreader bar</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-04-24</td></tr>

<tr><td><b>Updated:</b></td><td>2020-08-27</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-02 16:20:28</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>6</td></tr>

<tr><td><b>Words:</b></td><td>5,954</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/23822449</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/SinQueen69/pseuds/SinQueen69</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Most know Derek as the stoic CEO of Hale Enterprises, but Stiles knows better.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Derek Hale/Stiles Stilinski</td></tr>

<tr><td><b>Series:</b></td><td>Requests [73]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/1618726</td></tr>

<tr><td><b>Comments:</b></td><td>11</td></tr>

<tr><td><b>Kudos:</b></td><td>561</td></tr>

</table>

<a name="section0001"><h2>1. Chapter 1</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>“I wonder what those stuffy board members would say if they could see you now Mister Hale. Bent over your own desk and taking it up the ass like a bitch in heat.” Stiles purred as he slapped both of Derek’s ass cheeks, watching the plump flesh jiggle and listening to the little whine Derek gave in reply. </p><p>“You’d like that wouldn’t you Mister Hale, let the whole world know that you bend over for me, that you beg for me to fuck you like a slut.” Stiles carried on as he tugged on the CEO’s tie that was acting as a makeshift leash. Derek gasped as he was forced to arch up off the surface of his desk and Stiles mouthed up the column of his neck, his hips never stopping as he rocked in and out of Derek’s hole. Derek spread his legs a bit wider and pushed back to meet each of Stiles’ thrusts. </p><p>“Yes Sir,” Derek whimpered as he clenched around his lover’s cock at Stiles’ words. </p><p>“This is the reason you asked me over here for lunch, you were so desperate for my cock in your ass that you couldn’t make it through the work day.” Stiles breathed out as he snapped his hips forward, adding more force than he had been using and laughed when Derek gave a little yelp as he was pushed up onto his tiptoes. </p><p>“My greedy little slut,” Stiles hummed pleased with how the tips of Derek’s ears were turning pink and he nipped at them as he smoothed his hand over the bulge in Derek’s jockstrap, groping the other’s erection through the fabric. </p><p>“You want to go back into that meeting with my cum dripping down your thighs. Having it there will ground you and remind you that you belong to me.” Stiles knew his words were getting to Derek as the CEO whimpered and gasped as his body began to tremble. </p><p>“Ask nicely and I may do just that,” Stiles decided as he teasingly snapped the band of the jockstrap earning a breathy moan as Derek jerked back against him. </p><p>“P-Please Sir, will you come in me before you go?” Derek’s voice was hitching as he spoke and his words panted out as Derek clung to the edge as he rocked between fucking himself against Stiles’ cock and rubbing himself against Stiles hand. </p><p>“That’s my greedy slut, always ready and eager for a load in his ass.” Stiles crooned as he nipped at the skin of Derek’s throat and released his hold on Derek’s tie. Derek let out a noise as Stiles pushed him down flat onto his own desk and began to really pound into him. Derek muffled his moans and greedy noises in his arms as he lifted his hips to allow Stiles to penetrate him deeper. </p><p>Stiles plastered his front of Derek’s back and twisted the CEO’s head to the side so they could kiss messily as Stiles buried himself balls deep inside of his submissive and spilled his load inside of Derek’s clenching hole. Derek whined into the kiss before it broke and Stiles slipped out of Derek’s well used and cum filled hole. </p><p>Stiles’ licked his lips at the sight and couldn’t resist from smacking Derek’s bubble butt once more before he righted his clothes and tucked himself away. He watched as Derek’s hole clenched as he tried to keep Stiles’ release inside of him. Stiles moved around the desk and knelt down next to it and ran his fingers through Derek’s hair, getting a dopy smile in return.</p><p>“If you be good for the rest of the day and come home on time I’ll reward you okay sweetheart.” Stiles said steadily as Derek’s eyes slowly cleared and he nodded silently, knowing full well if he disobeyed that order he was be punished instead of rewarded. </p><p>“We should really keep a plug here for you for our lunch meetings, but then again where is the challenge in that?” Stiles laughed slightly and leaned up to kiss Derek tenderly, hand still stroking his hair and over the back of his neck. </p><p>“I’ll see you at home?” Derek asks once Stiles helps him upright and fixes his clothes with gentle touches.</p><p>“Can’t wait,” Stiles said honestly and with one final kiss the smaller man was gone leaving Derek in his suit not one hair out of place but with Stiles’ cum rolling down his inner thighs.</p>
  </div></div>
<a name="section0002"><h2>2. Chapter 2</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Summary for the Chapter:</b><blockquote class="userstuff">
            <p>anon asked: How about Derek blindfolded and gagged with his arms and legs bound to a chair naked while Stiles edges him? Stiles brings Derek close to orgasm but delays him multiple times. Maybe body oil and nipple play?</p><p>+</p><p>Anon on Request Form: Sterek and body/muscle worship</p>
          </blockquote></div><div class="userstuff module">
    
    <p>“Well Mister Hale, I have to say. This is a damn good look on you.” Stiles purred as he coated his hands in warm oil as he hungrily looked at his submissive. </p><p>The older man strained lightly against the strong, leather cuffs that were keeping his wrists and ankles locked to the wooden chair’s arms and legs. Derek turned his head to the side, blinded by the dark fabric that was tied tightly around his head and already a string of drool was escaping his mouth that was stuffed full of a ball gag. </p><p> “All tied up, like a present for me to do whatever I want to with.” Stiles mused as his oil-slick hand smoothed over Derek’s erect cock, smile widening as the older man’s cock twitched and jerked under his slow, light strokes and Stiles loved the way it leaked a fat bead of pre-cum when Stiles fondled the CEO’s balls. </p><p>Derek’s hips jerked repeatedly as he felt his balls beginning to draw up as his orgasm began to crest. Derek suddenly cried out behind the gag when suddenly Stiles’ hand and his mounting pleasure disappeared. </p><p> “None of that Mister Hale, you don’t have my permission to come… You won’t be getting that tonight,” Stiles’ breath was hot against Derek’s ear and his words sent waves of arousal and heat through the CEO’s body. </p><p>Stiles didn’t touch him at all until Derek’s cock had settled down so he was only half-hard before those talented, warm hands were back. Derek squirmed against the cuffs as Stiles caressed and rubbed at every part of his body except his cock and balls. Hell, Stiles even rubbed the body oil into the soles of his feet. </p><p>Derek thrashed and moaned when suddenly his cock was engulfed by Stiles' mouth. Stiles' hands gripped his hips firmly, keeping them pinned to the chair as he lazily moved his mouth up and down the CEO’s shaft. Derek was all but vibrating as he bit at the rubber of the ball gag in his mouth, mentally cursing the blindfold that stopped him from seeing what Stiles looked like while sucking his cock. </p><p>Derek fought back a sob when suddenly that wonderful wet heat was gone when Stiles pulled back a few moments before Derek was going to come. He hazily remembered Stiles' promise of him not coming that night and wondered how many times Stiles was going to deny him. </p><p>Stiles once again didn’t touch him until his cock had settled down. Then the younger man straddled him and slender fingers plucked and flicked Derek’s nipples, rubbing more body oil into the sensitive area. </p><p>Derek let his head fall to the side with a quieted moan as he was forced to arch his chest when Stiles pulled on the pebbled nubs until they were sore and peaked stiffly. </p><p> “I love your nipples Mister Hale, so big and round. Perfect to play with.” Stiles praised as rubber suddenly clamped down around the peaks making Derek cry out from behind the gag, noting that his cock took interest in the sudden shock of pain. </p><p>Stiles stilled, obviously noticing Derek’s reaction and somehow Derek knew that Stiles was smirking knowingly. Stiles waited just long enough before he tugged on the nipple clamps and chuckled when Derek’s cock filled again.</p><p> Derek lost track of how many times Stiles did this, forcing him to the edge and then letting him settled back down just from playing with his clamped nipples. It was humiliating and wonderful all wrapped into one. </p><p>“Oh Mister Hale, I can’t wait to see your pretty cute blush when I show you the picture I took of you before. I can’t wait to see your cock chub up when you realize what colour you’re decorated in, such a pretty little slut for me.” Stiles praised, dragging his index finger over the line of drool that decorated Derek’s chin before lewdly wiping it in a line over Derek’s cheek. </p><p> “You’ve done well for me tonight Mister Hale, coming up to that edge so many times and yet not spilling a single drop. Such an obedient little slut for me,” Stiles praised again as he twisted the clamps making Derek keen behind the gag and hips jerk when another bead of pre-cum slid down his shaft. </p><p> “Seeing you like this… It really gets me hot Mister Hale,” Stiles panted as the sound of skin sliding on skin filled Derek’s ears and the way Stiles was shifting on his lap clued Derek in. Derek felt his ears and cheeks heat up when he realized Stiles was jerking off from his place on his lap.</p><p> “Mmm,” Stiles moaned out as something hot and wet splattered over Derek’s stomach and rolled down to pool just above his cock.</p><p> “Such a pretty little slut and you’re all mine,” Stiles said pleased as he kissed Derek, uncaring of the ball gag and Derek moaned into it. He loved giving up control like this to Stiles and found it so hot when Stiles got off on it just like Derek did.</p>
  </div></div>
<a name="section0003"><h2>3. Collar</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Summary for the Chapter:</b><blockquote class="userstuff">
            <p>Stiles takes Derek shopping for a collar</p>
          </blockquote><b>Notes for the Chapter:</b><blockquote class="userstuff"><p>Tags: Dom/sub, Dom Stiles, sub Derek, CEO Derek Hale, humiliation kink, collar, possessive Stiles, light pet play, foot humping</p></blockquote></div><div class="userstuff module">
    
    <p>“What are we doing here Sir?” Derek kept his voice soft and quiet as he cut the engine of his Lexus and glanced up at the pet store. </p><p>“We’re here to get you your collar Mister Hale,” Stiles purred as he leaned over to Derek, kissing his cheek as his hand coped a feel of Derek’s cock through his jeans. Derek felt blood rush to both his cock and cheeks as the realization clicked in. </p><p>Derek took a moment to will down his growing erection as Stiles slipped out of the high-end car Derek could afford as a CEO before following when he looked decent. </p><p>Stiles laced their fingers together as they entered the pet store and towed the older man over to the collar section. </p><p> “You don’t have to worry about a thing babe, I’ll take care of everything. Just stand there and look pretty,” Stiles winked with a sneaky swat against Derek’s ass that just made Derek blush brighter. Derek did his best to not fidget as Stiles took his time, looking at each collar and humiliation coiled in his stomach with each passing minute. </p><p>It sank in that Stiles was getting his collar from the pet store like he was nothing more than the younger man’s pet and that sent a flush of arousal through his body that he fought back. </p><p>“Aha!” Stiles beamed as he held up a bright pink collar with small, round silver studs embedded along the leather. Derek felt his ears burn as he realized the pink matched the pink leather that had coloured the restraints he had been wearing in their last session. Stiles had planned ahead of time to make sure everything would match. </p><p> “Perfect! Come on let’s go buy it.” Stiles tugged Derek over to the cash, snatching a matching pink leash on the way and Derek knew his blush was only deepening. </p><p> “Would you like an engraved tag for the collar for an extra $10?” The female behind the cash chirped at them.</p><p> “That would be wonderful!” Stiles chirped back as he slipped his hand into Derek’s back pocket to slyly grope at his submissive’s ass. Derek had to swallow down his reaction to the touch as the cashier picked up a heart-shaped tag, clearing thinking it would be perfect with the pink leash and collar. </p><p> “What’s your pet’s name?” She asked as she positioned the tag in the engraver. </p><p> “Derek,” Stiles said smugly and while the cashier quirked an eyebrow she put in the name. </p><p> “When I got my pet I thought he was a stud, but it turned out he was a bitch, you know what I mean? The name was stuck by the time I figured out it!” Stiles said conversationally and Derek felt his cock traitorously twitch and he had to keep his eyes turned down as he fiddled with his wallet. </p><p> “Oh, I totally understand!” The woman laughed as she finished putting Derek’s name on the tag and packed it up alongside the collar and leash. Derek was glad he could tap his card to pay, not wanting the woman to see his name and maybe put two and two together. </p><p>Stiles and the woman cheerfully said goodbye to each other and Derek all but sank into the driver's seat of his car as Stiles lazily stroked the back of his neck.</p><p> “Humiliating enough for you Mister Hale?” Stiles inquired in a smooth voice, eyes dark as the tag clinked against the collar in the bag.</p><p> “Very, thank you, Sir.” Derek breathed out allowing his cock to stiffen up the way it had wanted to the whole time he was in the store. Stiles kissed him swiftly before pulling on his seatbelt smugly. </p><p> “Good, I’m glad. When we get home I want you naked and kneeling for me in the bedroom, I want to collar you right away.” Stiles instructed before propping his chin upon his hand as he gazed outside his window.</p><p> “Yes Sir,” Derek murmured as he pulled his Lexus out of the pet store parking lot. </p><p>It felt like a year before they finally made it to Derek’s penthouse. Derek gave Stiles a small kiss before hurrying off to comply with his Dom’s orders. Derek took a few deep breaths once he was kneeling naked in the master bedroom, waiting for Stiles to join him.</p><p>Stiles joined him a minute later, clad in tight black leather pants and shining black knee-high boots that had Derek’s mouth-watering and bare cock twitching. Derek tipped his head back to offer Stiles his neck silently as Stiles held up the pink collar, the heart tag with Derek’s name dangling from the front. </p><p> “Such a good boy,” Stiles praised as he locked the pink collar into its proper place around Derek’s throat. It felt a bit odd but comfortable in a way Derek didn’t expect. </p><p>“Thank you, Sir,” Derek whispered, suddenly feeling a bit overwhelmed and fully aroused at the mere act of Stiles putting this pet store collar around his throat. Stiles traced the collar before tipping Derek’s head back further so they could look at each other properly. </p><p> “It suits you,” Stiles said simply and Derek couldn’t swallow down the whimper at the simple statement, his cock jerking from between his thighs. Derek gasped when cool leather of Stiles’ booted foot nudged against his balls before sliding up the older man’s shaft. </p><p> “You’ve been like this since we left the pet store and yet you haven’t touched yourself once,” Stiles observed.</p><p> “You didn’t give me permission to do so Sir,” Derek swallowed, adjusting to the way his Adam’s apple pressed against his collar and how he found himself desperate to grind against Stiles’ foot. </p><p> “You’re truly turning into an obedient submissive for me Mister Hale, I’m very proud of you.” Stiles crooned, pleasure shining in his eyes and it made Derek straighten up in pride as well. </p><p> “Thank you, Sir,” Derek’s words trailed off into a gasp when Stiles applied pressure to his balls with the toe of his boot, Derek was trying very hard to squirm as his cock throbbed.  </p><p> “You deserve a reward,” Stiles mused as he rubbed Derek’s balls with his foot as he thought. </p><p> “You may come if you can get off while humping my boot,” Stiles decided with a smirk on his lips as Derek’s eyes darkened and a small noise escaped his mouth as Stiles established his foot on the floor between the older man’s thighs. Derek glanced up at Stiles once before he let his head drop back down and he jerked his hips forward, dragging his cock and balls over the polished leather of Stiles boot.</p><p>A moan spilled from his lips at the sudden, delicious friction and his hips jerked forward again and again. Derek ended up clinging to Stiles’ leg as he panted and gasped as he humped the younger man’s boot like a dog, but Derek was too far-gone to care as pleasure sparked through his body. </p><p>Derek bowed his head back; eyes squeezed shut as he let out a long groan as he came, spilling his release over his Dom’s black leather boots. </p><p> Derek slumped against Stiles’ strong leg, gasping for air and he drifted when as he felt a familiar hand stroking his hair. Perhaps the collar from the pet store was a good fit for him, it belonged on him in the same way he belonged to Stiles.</p>
  </div></div>
<a name="section0004"><h2>4. Request Form Anon</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Summary for the Chapter:</b><blockquote class="userstuff">
            <p>Anon from my request form wanted: Can we have bottom Derek with a praise kink? Could include Dom ! Stiles and some bondage or something lazy morning and romantic? Please and thank you! (sorry if its tame)</p>
          </blockquote><b>Notes for the Chapter:</b><blockquote class="userstuff"><p>Tags: Dom/sub, Dom Stiles, sub Derek, CEO Derek Hale, bottom Derek Hale, collar, bondage, praise kink, spreader bar, anal sex, anal fingering, begging, creampie</p></blockquote></div><div class="userstuff module">
    
    <p>Stiles ran his left hand down Derek’s spine; a lazy smile on his lips as he adjusted the angle of his right hand, drawing a low moan from the older man sprawled out below him on the bed. Stiles curled his slender fingers before pressing at a small nub that had Derek gasping and lifting his hips off the bed briefly. </p><p>“None of that Mister Hale,” Stiles purred as he slowly squeezed his pinky into Derek’s hole, grinning at the whine of pure need the CEO let out at the action and the new stretch. </p><p>Derek twisted his wrists, trying to grab onto something as his Dom played with him, but the metal spreader bars that were attached to his pink leather cuffs prevented that, keeping his arms immobile above his head. </p><p>“Ssh Mister Hale, you’ll get what you want soon enough.” Stiles shushed the CEO, dropping kisses on the skin around the bright pink dog collar that was proudly displayed from Derek’s neck. </p><p> “P-Please Sir,” Derek breathed out as he lifted his hips, his cock hard and leaking from where it was trapped between his stomach and the soft sheets of the bed. </p><p> “What was that Mister Hale? Was that a plead?” Stiles asked in faux surprise as he curled his four fingers inside of Derek’s hot, tight channel loving the moan it earned him. </p><p>“Y-Yes Sir, please, please.” Derek nodded against the pillow his face was buried against. The CEO’s mind was blank and his whole body was engulfed in desire and need, he needed Stiles, he needed to have his Dom inside of him, filling him and dousing the burning arousal in his veins. </p><p> “Since you asked so nicely,” Stiles chuckled fondly mostly to himself as he slowly removed his four fingers and instead lubed up his cock before lining up to the older man’s loose hole. </p><p> “I do love it when you beg Mister Hale,” Stiles whispered in Derek’s ear as he swiftly thrust his whole length into the CEO, grinning sharply at the loud cry Derek gave in reply. </p><p> “You feel so good around me Mister Hale, so damn hot and tight. I could stay inside of you all day,” Stiles panted out as he began to shallowly thrust in and out of the older man, drawing out the cutest noises. Derek twisted his wrists against the cuffs and spreader bar as he gasped into the pillow as the younger man’s thrusts began to get harder and deeper. </p><p> “Do you know why I collared you, Mister Hale?” Stiles curled one hand around the collar around the CEO’s throat as he ground his cock against Derek’s prostate listening to the high-pitched whine he got in reply. Derek bit back a sob at the sensations and shook his head when Stiles repeated the question in that same soft, knowing voice. </p><p> “I collared you because you Derek Hale, are so good. You are such a good boy, all you needed was someone to show you that.” Stiles said bluntly as he lifted Derek’s hips off of the bed, driving deeper into the older man with a moan. </p><p>Derek began to shake as Stiles repeated that Derek was a good boy over and over, each time he was sheathed inside of his ass he said it. Derek squeezed his eyes closed as he panted and mewled under all the wonderful praise and attention. </p><p>Derek wailed when Stiles jerked him off and nailed his prostate on the next thrust. Derek came like that, Stiles’ panting out his praises through the whole thing as Derek’s body shook apart with his orgasm. </p><p>Derek felt hazy as he collapsed on the bed, totally spent and boneless. Derek whined when he felt Stiles pull out of his sore ass, letting hot trails of cum drip down his thighs and balls. </p><p> “You’re my good boy Derek, never forget that,” Stiles whispered as he undid the leather cuffs and cuddled Derek close, one hand resting on the collar that marked Derek as his.</p>
  </div></div>
<a name="section0005"><h2>5. BDSM Club</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>“Are you ready?” Stiles asked as he gave Derek a once over in the ready room that was the last barrier before they entered Midnight. Stiles’ was fiddling with the pink leather leash in his hands as Derek turned to face him properly.</p><p>“Yes Sir,” Derek wet his lips as he lowered his eyes submissively. Stiles straightened up on reflex when given the submissive look and fell into his headspace. </p><p>“Kneel,” Stiles said firmly and slowly inhaled when Derek gracefully fell to his knees, hanging his head down, which gave Stiles a good view of the pink collar and heart tag that was locked around his throat. </p><p>“Head up,” Stiles instructed and waited until Derek was looking up at him and hooked one end of the pink leash through the silver D-ring at the front of Derek’s collar. </p><p>“Stand,” Derek rose up, towering over Stiles as he normally did but they both knew who was in charge right now. Stiles took in the pink leather harness that framed the larger man’s chest and shoulders and his groin was encased in tiny black leather shorts that left nothing to the imagination. Stiles himself was wearing leather pants, boots and nothing else. Stiles looped his end of the leash around his wrist and tugged on it until Derek bent down. </p><p>“Let’s have some fun,” Stiles whispered as he hooked his hand around the back of the larger man’s neck and kissed him passionately. </p><p>“Yes Sir,” Derek hummed, a pleased flush on his cheeks when their kiss broke. Stiles shoved his hands into his pockets and walked out of the room into the Dungeon itself with Derek shuffling a step or so behind him like an obedient submissive. </p><p>Midnight lived up to its name, it was a dark sprawling space under the club above it and it was a mix of stone and plushness. There were smaller sections throughout the room, each one having a different scene happening while a circular bar in sat in the middle of the room. Stiles headed towards that, eyes darting every which way to take in everything he could. He knew Derek was doing the same and it must be overwhelming. </p><p>Stiles settled on a bar stool and tugged lightly on Derek’s leash and smiled when the man instantly knelt at the foot of the stool and rested his head against the younger man’s thigh. Stiles rested his hand on the top of Derek’s head and motioned to the bartender with his other hand. </p><p>“Hello handsome, what can I get for ya?” The woman in a purple leather corset asked cheerfully, eyes tracing over Stiles and then down over Derek’s kneeling form. </p><p>“Just water please,” Stiles wanted to have a clear head.</p><p>“Coming right up!” She said as she added ice to a tall glass and then poured water into it before setting the glass in front of Stiles with a wink. </p><p>“Thank you,” Stiles sipped his drink as he looked around.</p><p>“First time here handsome?” The bartender asked carefully. </p><p>“Yes, we know the rules but seeing everything in person is a bit overwhelming,” Stiles admitted as he began to pet Derek’s hair, knowing it helped ease the larger man’s nerves that he usually hid so well. </p><p>“Take your time, see what strikes your fancy and if you want my opinion, don’t use any of the scene area’s tonight. Stick with what the two of you know, just to get the hang of being here and then branch out.” The bartender advised and Stiles raised his glass in thanks as she was beckoned to the other side of the bar. </p><p>“Let’s go find a seat,” Stiles slipped off the stool and waited until Derek rose to his feet behind him before starting over to a plush chair in an empty lounge area across the room. Stiles settled in the comfortable seat and studied Derek who was standing still in front of him, head down still. </p><p>“I want to rest my feet for a bit I think,” Stiles decided as he tugged on the leash and smiled as relief flashed across Derek’s face. The larger man sank onto his hands and knees in front of the chair, head bowed low and body tense as Stiles lifted his feet up and rested them on Derek’s back, using the man as a footrest. </p><p>Stiles sipped his drink as he sank into the presence Midnight gave off, even with grunts, gasps, and cries echoing from the nearby scene areas the thrill hummed in Stiles’ veins. </p><p>“Beautiful submissive you have,” A man commented as he and his own partner settled in a chair only a few down from Stiles and Derek. The man’s partner settled on his lap, nuzzling his neck lovingly.</p><p>“Thank you, you as well,” Stiles said politely when spotting the partner’s collar. The man lifted his glass to Stiles before turning his attention the squirming man on his lap and Stiles turned his own attention to the man below his feet. </p><p>Derek seemed at ease and relaxed even as his body shook with small tremors at being forced to stay still under the weight of Stiles’ feet. Stiles’ eyes were caught by how dull his boots looked and frowned. He had Derek polish them a week ago, but already they were already dulled and an idea sparked in the brunet’s mind. </p><p>Stiles lifted his feet off of Derek’s back and waited until the older man straightened up so he was kneeling normally. Stiles placed his feet on Derek’s thighs and inspected the man’s face and smiled at what he found. </p><p>Derek’s eyes were blown wide and hazing over, his cheeks were a nice shade of pink that darkened his skin and he was breathing quietly through parted lips as he slowly blinked up at Stiles. </p><p>“I was just noticing that my boots have lost some of their shine,” Stiles explained slowly as he shifted his right foot up until it was lightly pressing down at the bulge in Derek’s leather shorts. Stiles smiled lazily as Derek inhaled sharply and moved his foot in small circles, applying more pressure each time until Derek was clutching at his ankles behind himself and giving short jerks of his hips up into the friction.</p><p>“I think they are in need of a touch up don’t you?” Stiles said as he propped his chin on his palm, elbow resting on the armrest of the chair as Derek’s breathing hitched and he looked up at Stiles with wide eyes. </p><p>“First, I want to watch you come with my boot on your cock like this.” Stiles decided as he pressed down on Derek’s crotch with firmer pressure, smiling when Derek gave a high-pitched whine from the back of his throat. Derek let his head fall back as he began to hump almost desperately against the underside of Stiles’ boot. </p><p>Stiles felt his own cock begin to swell up in his leather pants at the sight of Derek rubbing himself against his boot without a care in the world. He was so focused on getting off with Stiles’ permission that the people in Midnight didn’t matter at all to him, was extremely hot. </p><p>Derek lifted his head up just enough to look at the blond, his eyes fluttering as his Adam’s apple bobbed as he moved his hips harder. Stiles leaned forward, tugging the leash as he did. Derek was tugged upright and Stiles tangled his slender fingers in his hair and gave a shark-like smile before uttering a single command.</p><p>“Come,” </p><p>Derek was gone the moment that word was uttered, his hips stuttering against Stiles’ boot and his world whited out for a moment. His orgasm left him gasping and trembling, as he felt his own cum spread across the front of his leather pants, it was sticky and hot against his softening cock and he shuddered when Stiles pressed down against it again. </p><p>“Good boy,” Stiles crooned as he released his hold on Derek’s hair and leaned back in his chair watching as Derek slumped slightly like his strings had been cut. Derek was glad he was allowed a moment to regain his senses before he shuffled back just enough to let Stiles’ feet fall from his lap and he bent himself over so his chest brushed the ground and he lapped at the toe of Stiles’ right boot. </p><p>“I want to see them shine,” Stiles said as he watched as Derek’s tongue darted out and made long, board strokes over the leather repeatedly. Stiles hissed lightly as he unzipped the front of his tented leather pants, allowing his weeping erection to spring free and he loosely coiled his fingers around the heated flesh. </p><p>Stiles lazily stroked himself as he watched Derek work on cleaning his boots; the larger man had finished the right one and was working diligently on the left one now.</p><p>“So obedient and eager,” Stiles commented knowing that the flush on Derek’s cheeks had darkened at the praise, as they tended to do. It wasn’t long before Derek was back in his upright kneeling position, chin and lips wet with his own saliva and Stiles lifted up one foot at a time and inspected the new shine that the leather was given. </p><p>“You did well, my good boy deserves a reward. Mouth open and eyes closed,” Stiles shuffled forward on the chair, holding his cock and saw a spark of need in Derek’s eyes before the man did as he was told. Stiles grunted and moaned lowly as he quickly jerked himself off and watched through half-lidded eyes as his cum painted Derek’s face, obviously marking him as Stiles’.</p><p>“Such a pretty sight,” Stiles crooned as he grabbed some nearby tissues and wiped his now limp cock free of his release and zipped himself back up. He settled back in the chair and tugged on Derek’s leash until the large man was curled up between his legs and had his cum-stained face resting against his thigh once again.</p><p>“Thank you, Sir,” Derek spoke for the first time in a while, his voice hoarse and rough as he nuzzled against Stiles’ thigh making the young man smile pleased.</p>
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<a name="section0006"><h2>6. Final: Object Insertion [Prompt Fill]</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Summary for the Chapter:</b><blockquote class="userstuff">
            <p>Anon’s from my request form wanted: <br/>Can you write a story with Bottom Derek and orgasm denial where Stiles loves stuffing him with different things? It started out with sex toys but escalated to things like his baseball bat? Or any other object you have in mind<br/>+<br/>I don’t really care what pairing but I’d like to see some overstimulation and large object insertion. Thank you!</p>
          </blockquote></div><div class="userstuff module">
    
    <p>“What do you think Mister Hale, was that toy big enough for your greedy hole?” Stiles asked curiously, hand on Derek’s slightly bugling stomach as he slowly eased the dildo with the girth of a soda can out of his now gaping, messy hole. </p><p> “So good Sir,” Derek let his head fall to the side, glad for the extra pillow Stiles had stuck under his head. Derek whined in loss when the rest of the dildo slipped out of him with ease, leaving him so damn empty. </p><p> “I’m empty again Sir, it wasn’t enough, please Sir, do we have anything bigger?” Derek pleaded, desperate to be filled again, desperate to feel that burning stretch that he had been craving so much of lately. </p><p> “I may have something, but it’s extreme, are you ready for that Mister Hale?” Stiles said slowly as he gently petted at Derek’s well-stretched rim, noticing that it didn’t even flex at his touch. Stiles licked his lips, Derek’s hole was so, so close to being a perfectly ruined one and obviously, Derek wanted that. </p><p>“What is it, Sir?” Derek asked curiously, curling his toes and fingers from their spread eagle formation on the bed, his hips propped up high by a few pillows to keep him comfortable as they worked towards ruining his hole properly. </p><p> Stiles dropped a kiss to Derek’s hip before he slipped off the bed and returned in a moment, twisting his baseball bat around his hand with a wicked smile on his lips.</p><p> “This big enough for your greedy hole Mister Hale?” Stiles tapped the metal bat against his flat hand and Derek moaned out of want, hips jerking up and gaping hole trying to clench. </p><p> “Yes Sir, please may I have it? Will you please use your bat to ruin my hole, Sir?” Derek pleaded, consumed with the need to take that large bat in his ass. </p><p> “You will safe word if it’s too much, am I understood, Derek?” Stiles said seriously, cupping Derek’s chin to look at him dead on.</p><p> “Green, I understand Sir,” Derek promised, he knew how to push his limits, not break them. </p><p> “Good boy,” Stiles crooned, jingling the dog tag on Derek’s hot pink collar before he sat back down on the bed, applying basically a whole bottle of lube to the fat end of the bat while Derek watched while panting quietly. </p><p>“Ready?” Stiles sounded as breathless as Derek felt as he nudged the massive blunt end of the bat against Derek’s gaping hole. </p><p> “Yes Sir, oh, oh, oh! Yeesss!” Derek gasped out, eyes rolling up into his skull as his body trembled as the massive end of the bat was gently pushed into him. Derek went limp and drool dripped down his chin from the corners of his mouth as he stared unseeing up the ceiling as Stiles eased more and more of the bat into his ass. </p><p> “So good Sir, it’s so big and so wonderful,” Derek babbled as the familiar burning stretch appeared again as his rim fluttered around the thick, unyielding metal of the bat that was now shoved so deep inside of him that his stomach was bugling on the edge of obscenely. </p><p> “Look at your greedy hole, it’s just swallowing every inch of this bat up. You’re going to be properly ruined when we finish here tonight, such a good boy.” Stiles praised as he slowly thrust the bat in and out of Derek’s ass as he jerked himself off watching how wide his submissive’s hole had been stretched. The bat soon was moving in and out of Derek with ease and a smooth gliding motion. </p><p>Stiles stopped touching himself to jerk Derek off again, needing to wring one more orgasm out of Derek while he had the bat buried deep in his ass. Derek sobbed at the new stimulation on his sensitive cock, he writhed as his Dom milked his cock of any cum it had left while the bat pressed against his prostate and opened him wider than anything else had. </p><p>Derek arched up off the bed when his cock spurted little drops of cum as his orgasm exhausted him in a way he hadn’t felt before. Derek collapsed down gasping for breath and he felt floaty, but oddly grounded by the bat was that was now sitting in his ass. </p><p> “Good boy, Mister Hale,” Stiles’ praise was the last coherent thing he heard before his mind turned to fuzzy contentment and his vision faded and Derek somehow knew that he would wake to a properly ruined hole and that was a wonderful thought.</p>
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